


Teaching Sam

by Dean_Winchesters_Impala67



Category: Supernatural
Genre: M/M, Masturbation, Oral Sex, Teaching Sam To Jerk Off, Underage - Freeform, Weechesters, Wincest - Freeform
Language: English
Status: Completed
Published: 2016-01-24
Updated: 2016-01-24
Packaged: 2018-05-16 01:40:19
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 2,024
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5808355
Author URL: https://archiveofourown.org/users/Dean_Winchesters_Impala67/pseuds/Dean_Winchesters_Impala67
Summary: <blockquote class="userstuff">
              <p>Sam woke up from his first wet dream. Dean gives him books on puberty, but when Sam try's to jerk off he fails. Dean then comes to the rescue.</p>
            </blockquote>





	Teaching Sam

**Author's Note:**

> I need to update my other story I know. But I had this in my mind so I wanted to post it.

The pleasure ripped through Sam's body in the split of a second. He jerked awake. Nightmare, was the first thought that came to his mind. Being fourteen made the nightmares worse. But he hadn't been crying. He had been sweating, laying on his stomach, his hand gripped the edge of the bed that was his. Dean was on his side sleeping. 

That's when Sam realized his underwear was sort of wet. Had he peed the bed!? Oh no, this couldn't be happening. 

"Dean," he said as he shook his brother to conscious. 

"What, What? I'm awake, Sammy are you okay," A groggy Dean asked. 

He let the 'Sammy' slide, "I think I wet the bed Dean." 

"I don't feel anything Sam," Dean looked at him serious. 

"It's just a little bit, I don't know Dean am I sick?" Sam asked, he thought maybe a ghost had done something to him on the last hunt. 

"Sam... I don't think you're sick. Go was off, put on some new underwear. We can discuss this tomorrow when it's not 2:30 A.M," Dean told him. 

Sam knew that if Dean didn't think it was a big deal that he wouldn't be in grave danger. He did as Dean said, easing off and putting a new pair of boxers on. 

"Get back in the bed, kiddo," Dean said. 

Sam did as he was told. Dean rapped his arm around Sam's waist, "Damn Sam your cold now," Dean muttered as he slipped out of consciousness and back into sleep.

When Sam woke up in the morning his boxers were dry. That he was thankful for. The rumble of water hitting the wall in the shower sounded. Sam got out of bed, and walked toward the shower door. 

He knocked on it, "Hey Dean can I come in." 

"Sure kiddo," Dean said over the water. He stuck his head—covered in shampoo— out of the curtain, "you alright?" 

"Just thinking..." Sam said letting his mind wonder to last night. 

"About last night?" Dean asked as he got back behind the shower curtain. 

"Yes... that's never happened to me before Dean," Sam said. 

"I know Sam, I know, give me three minutes. Go set on the bed," Dean told him, and Sam did as he was told. 

Sam sat on the edge of the bed. Dean came out a couple minutes later a towel hung low around his waist. He didn't even bother putting pants on as he sat next to Sam, he just kept the thin material around his waist. 

"Well Sam," he started. Sam noticed the faint redness on Deans cheek that kept getting redder, Dean hardly ever blushed, "You've finally became a man. Or at least a part of one." 

Sam was confused as the words fell out of Deans mouth. Dean could see the confusion written on Sam's face. So he spoke up, "dude you had a wet dream." 

Sam was confused still a wet what?

Dean could see Sam's face twist up into more confusion and this time annoyance was an additive. 

"Sam you have… you know touched yourself before right?" Dean asked. 

Sam looked at him with a duh face on, "not what I mean Sam." 

Dean got up letting the towel fumble to his feet—Sam knew Dean had no shame when it came to nakedness—Dean slid some boxers and a tight pair out jeans on. He didn't bother putting a shirt on. 

He was on the way of walking out the door, and stopped, "shirt he mumbled." 

Sam watched as Dean rushed to his duffel, grab a shirt that probably wasn't even clean. It was badly wrinkled. 

"I will be back in 20 minutes. Don't go anywhere. If dad calls I didn't leave you alone. I'm in the shower. I will call him when I get out. Got it?" Dean asked. 

Sam nodded. Dean walked out of the hotel forgetting shoes. He came back in. Told Sam not another word. Grabbed his shoes and walked out again leaving Sam to set on the bed and search his mind for anything references on the subject at hand. He knew nothing.

Right to his word Dean appeared twenty minutes later. He pointed at Sam when walked through the door, "when everything is done with what I'm about to show and give you I am going to kill you." 

Sam looked at him. Dean was blood red, his eyes had an annoyed look to them, but a sweet gentle tone to the green tent. 

Dean handed him books, "time for research. I want you to read these. Then do what it says. I will be back in exactly forty-five minutes. Please be finished by the time I get back done!" 

"Dean, what?" Sam asked as books were thrust onto his lap. 

"Bye Sam," Dean said and winked at him, "good luck!" He yelled as he walked through the door. 

Sam let out a string of normal teenage curses. He looked down at the books. They were about puberty. What to do during puberty. And Sex Ed 101. 

Sam went into research mode reading. He finished one book and was mortified but intrigued at everything. He finished all of the books and had an idea on what to do now. That book had a column on masturbation and the best way to tackle it. He looked at the clock. He still had twenty minutes until Dean would be back. 

He took off his clothes as the book said it was best to be comfortable. He lay on the bed his legs pulled up slightly and into a V-shape. He gripped his penis, and hissed at the feeling. He was not hard, but the book said I would take slight stimulation to get it to be in that state. 

He stroked from the head down to the base. It responded, but not like the book said. The book said stimuli would help. Paperview porn was on one of the channels. He knew because he read the TV guide. He didn't know at the time what porn was. 

He got up and flipped the TV on and found the channel. It was just something simple. A pretty blond and a plumber. They were still dressed. Sam watched as the tool each other's clothes off, and kissed each other. The plumber already had his hand up the girls skirt. 

As Sam watched he noticed that his penis was finally taking attention, it was only half hard, but with a little movement it got harder until it was fully hard. 

Sam kept a lose grip on it just stroking up and down. It was starting to hurt, and was making him angry because it started to hurt even more. He quit stroking. He put a pillow on his lap. Tears stung his eyes and started rolling down his face as he watched how pleasure full the couple on the screen was feeling. He didn't realize he had lost track of time. 

The hotel door opened, Sam didn't have time to move as Dean walked in with a smile on his face. When he saw the state Sam was in his face fell. The tears came even stronger for the split-second that Dean stared at him. He gripped the pillow tighter and pushed it down which made him hiss again at the friction. 

"What happened?" Dean asked incredulously. 

"I don't know. I couldn't get hard until I turned that on. Then when I got hard it started hurting so bad that I had to stop!" Sam explained through the tears and the loud moans that was coming from the tv. 

"Wow, awesome Sam." Dean said sarcastically which made Sam start crying again. "Sam no. I was kidding..." 

Dean had made his way setting down beside Sam on the bed. Sam gripped his shirt and cried into it as Dean held onto him. Neither one of them was paying attention to Sam being naked. 

Sam got up the courage to ask, "will you help me?" He hiccuped after. 

"Sam-," Dean started, "I don't think that's a good idea."

"Please Dean! It's still hurting," Sam said. 

Dean removed the pillow from Sam's lap. His dick wasn't half-bad in size. Right now Dean was bigger, but Sam would out grow him soon. Sam's dick stood hard up against his stomach. 

Dean got up, "I'll be right back." He told Sam as he got up and wet a rag in the sink. He came back over to the bed and whipped Sam's face cleaning and cooling his brother down. 

Sam didn't say anything when Dean climbed back into the bed with him. 

Dean the whispered into his ear, "I'm gonna help you." That's when he claimed Sam's mouth. Sam had never really kissed anyone. Maybe a cheek, but that's all. Sam gasped a little when Dean but his lip. This allowed Dean to slide his tongue slightly into Sam's mouth teasing. Sam had became responsive, humphing Deans leg slightly. Sam didn't even notice. 

"Sam I'm gonna touch you now," Dean told him. 

"O-" he cleared his throat, "okay." 

Dean slid Sam into his lap and pulled his legs up so Sam could lean back while he straddled Dean. 

Dean tweaked Sam's nipples a bit before leaning down and sucking the right one into his mouth. Sam moaned slightly. Nothing major like what was going on, on the Tv. Dean raised up grabbing the remote. He muted the Tv, "can't have them taking the sounds away from you," Dean said and flipped him and Sam over. Sam shrieked lightly. 

Dean kissed Sam again and finally gripped Sam's cock. Sam moaned louder than the first time. Dean took his other hand and fondled Sam balls. Sam jerked up. 

"This is much better, thank you Dean," Sam said. 

That's when Dean sped up a little more. Sam wasn't going to last much longer so he wasn't going to tease any longer. 

That's when Sam looked at the tv. There was no sound, but what was on the tv took his breath. 

"D-Dean what is she doing?" Sam asked. 

Dean slowed his stokes and looked at the tv. The blond was sucking the plumber down into her throat. 

"She's sucking him off Sammy, you know oral sex?" Dean asked. 

"Y-Yeah, has… has anyone ever done that to you," Sam answered and asked. 

"Yeah once baby boy," Dean told him. 

"O-oh," Sam chocked out, "Does it f—moan— feel good?" 

"It does," Dean said. 

"Close your eyes Sam," Dean said. 

Sam did as he was told. Dean slid down the bed. He had never done this before, but Sam deserved this for all his troubles. 

He touched his tongue to one of Sam's balls. And Sam jerked his eyes flying open. Before he could ask what Dean was doing, Dean licked a strip up Sam, when he got to the head he rolled his tongue around the top licking a bit at the slit. Sam groaned and thrusted up. 

"Sam I've never done this before. I will let you fuck my mouth another time, if you don't choke me to death," Dean said. There would be a next time? Dean wasn't thinking about that right now. 

Sam nodded. He pulled his hips back down. 

Dean then engulfed Sam Dick into his mouth. The four and a half inches wasn't as hard as he thought to swallow. Dean got maybe three or four up and down strokes before he heard the noise he know much to well from his own jerk off experience to know Sam was about to shoot. He was going to pull off, but the one he got the girl didn't pull off and it made it 50x better. 

Sam made another sound and he was coming. Dean knew that Sam couldn't help it when he jerked up. It was the first time that he had ever came. 

While Sam was elated into the bed with droopy eyes Dean slipped off the bed. He went off and jerked himself in that bathroom coming faster than he would ever admit. 

There would be a next time he decided.


End file.
